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Record Information
Version3.6
Creation Date2007-05-22 20:51:34 UTC
Update Date2016-02-11 01:07:27 UTC
HMDB IDHMDB06272
Secondary Accession NumbersNone
Metabolite Identification
Common Name5-Amino-2-oxopentanoic acid
Description5-Amino-2-oxopentanoic acid is a breakdown product of D-proline. D-proline is first converted to 1-pyrroline-2-carboxylic acid via D-amino acid oxidase, which then spontaneously breaks down into 5-amino-2-oxopentanoic acid.
Structure
Thumb
Synonyms
ValueSource
2-oxo-5-amino-PentanoateChEBI
2-oxo-5-AminopentanoateChEBI
2-oxo-5-AminovalerateChEBI
5-amino-2-OxopentanoateChEBI
5-amino-2-Oxovaleric acidChEBI
alpha-keto-delta-AminopentanoateChEBI
2-oxo-5-amino-Pentanoic acidGenerator
2-oxo-5-Aminopentanoic acidGenerator
2-oxo-5-Aminovaleric acidGenerator
5-amino-2-OxovalerateGenerator
a-keto-delta-AminopentanoateGenerator
a-keto-delta-Aminopentanoic acidGenerator
alpha-keto-delta-Aminopentanoic acidGenerator
α-keto-δ-aminopentanoateGenerator
α-keto-δ-aminopentanoic acidGenerator
a-keto-δ-aminopentanoateGenerator
a-keto-δ-aminopentanoic acidGenerator
Chemical FormulaC5H9NO3
Average Molecular Weight131.1299
Monoisotopic Molecular Weight131.058243159
IUPAC Name5-amino-2-oxopentanoic acid
Traditional Name5-amino-2-oxopentanoic acid
CAS Registry NumberNot Available
SMILES
NCCCC(=O)C(O)=O
InChI Identifier
InChI=1S/C5H9NO3/c6-3-1-2-4(7)5(8)9/h1-3,6H2,(H,8,9)
InChI KeyInChIKey=BWHGMFYTDQEALD-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as short-chain keto acids and derivatives. These are keto acids with an alkyl chain the contains less than 6 carbon atoms.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassKeto acids and derivatives
Sub ClassShort-chain keto acids and derivatives
Direct ParentShort-chain keto acids and derivatives
Alternative Parents
Substituents
  • Short-chain keto acid
  • Gamma-aminoketone
  • Alpha-keto acid
  • Alpha-hydroxy ketone
  • Ketone
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected but not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
  • Protein synthesis, amino acid biosynthesis
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
  • Peroxisome
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility56.1 mg/mLALOGPS
logP-2.5ALOGPS
logP-2.6ChemAxon
logS-0.37ALOGPS
pKa (Strongest Acidic)3.11ChemAxon
pKa (Strongest Basic)9.79ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area80.39 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity30.8 m3·mol-1ChemAxon
Polarizability12.59 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
  • Peroxisome
Biofluid Locations
  • Saliva
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
D-Arginine and D-Ornithine MetabolismSMP00036map00472
Fatty Acid Elongation In MitochondriaSMP00054map00062
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
    • Zerihun T. Dame, ...
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023870
KNApSAcK IDNot Available
Chemspider ID388519
KEGG Compound IDC01110
BioCyc ID5-AMINO-2-OXOPENTANOATE
BiGG ID36830
Wikipedia LinkNot Available
NuGOwiki LinkHMDB06272
Metagene LinkHMDB06272
METLIN IDNot Available
PubChem Compound439402
PDB IDNot Available
ChEBI ID49268
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in transferase activity, transferring acyl groups other than amino-acyl groups
Specific function:
Abolishes BNIP3-mediated apoptosis and mitochondrial damage.
Gene Name:
ACAA2
Uniprot ID:
P42765
Molecular weight:
41923.82
General function:
Involved in D-amino-acid oxidase activity
Specific function:
Regulates the level of the neuromodulator D-serine in the brain. Has high activity towards D-DOPA and contributes to dopamine synthesis. Could act as a detoxifying agent which removes D-amino acids accumulated during aging. Acts on a variety of D-amino acids with a preference for those having small hydrophobic side chains followed by those bearing polar, aromatic, and basic groups. Does not act on acidic amino acids.
Gene Name:
DAO
Uniprot ID:
P14920
Molecular weight:
39473.75
Reactions
D-Ornithine + Water + Oxygen → 5-Amino-2-oxopentanoic acid + Ammonia + Hydrogen peroxidedetails